


Adventures In Babysitting

by Phantomlimb



Category: Supernatural, Teen Wolf (TV)
Genre: ? - Freeform, Alternate Universe - High School, Babysitting, Dean and Kids, Dean is So Done, Derek Has Issues, Embarrassment, F/M, Funny, Funny Stiles, Humor, M/M, Second-Hand Embarrassment, The Hales Are Werewolves, Triggers, Werewolf Mates
Language: English
Status: In-Progress
Published: 2014-03-21
Updated: 2015-09-15
Packaged: 2018-01-16 10:59:11
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,195
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1344976
Author URL: https://archiveofourown.org/users/Phantomlimb/pseuds/Phantomlimb
Summary: <blockquote class="userstuff">
              <p>Dean needs the money to fix up his dad's old impala and the only way he'll be getting the dough is if he becomes a babysitter. He thought it would be a one time thing but the kid  he has to sit for is a force to be reckoned with.</p>
            </blockquote>





	1. Dean, I Didn't Know You Were A Sprinkler

 

It was spring break and Dean finally had the time to get around to doing his research for his dream car. After many a hour spent on the computer and flipping through the newspaper‘s ads, Dean found his results were conclusive to his earlier hypothesis: he was f _ucked._ He groaned and pressed his head against the dining room table. Money was tight in the Singer household and even if it wasn’t, Dean still wouldn’t ask his Uncle for a loan; a car wasn’t a necessity but _god did he want one._

The car on his mind was his father’s old Chevy impala. She was still a beaut but some of her parts had gone rusty and she definitely needed a tune up. Dean wanted to honor his old man somehow and what better way than through his father’s biggest achievement? H ~~ardy har har fuck you dad~~. He really wanted to fix the old girl up but God, the price was waayy out of his depth.

Dean groaned again.

“Boy, you best quit that or I’m gonna stuff a sock in it.”

Dean looked up to see his Uncle Bobby walking from the living room to the kitchen to grab a beer.

“Bobby, do you know anyone who’s selling car parts cheap?”

“No because _no one sells car parts cheap_ ,” Bobby said, sass strong in the air.

Dean would roll his eyes but he knew better.

“What’re you even doin that you need cheap car parts for anyway?”

“I wanna fix Baby up and make her look like new,” Dean said, knowing Bobby would be satisfied with that answer unlike Sam who would usually be digging for a deeper meaning to his actions.

“Well instead of looking for car parts why don’t you look for a job?” Bobby asked with a raised brow.

“Do you know anyone who’s hiring?” Dean asked with a sigh.

“No but I’ll keep my eyes out,” Bobby retorted as he walked back to his comfy set up in the living room.

Dean closed the computer and got up. There was no point in moping around so he decided to best spend his time fixing what he could of the car so with that in mind, he walked to their outside garage. There she sat, the Queen of the garage. He popped open her roof. An hour later, Bobby walked out and opened his truck’s door.

“Rufus is having a poker night and Sam’s sleeping over at Andy’s. You sure you gonna be okay here on your own?” Bobby asked as he put one foot in.

“Bobby, I’m sixteen, not six, I think I can handle being by myself,” Dean said from under the car.

“I know you can, just do you wanna be by yourself?” Bobby asked gruffly.

Dean rolled himself from underneath the car just so he could give him a _look._

“ _Have fun, Bobby,”_ Dean said with a smirk.

“Smart ass,” Bobby said fondly as he drove off.

Dean smiled to himself and continued to work on the car for the next hour. Oblivious to how long he had actually spent under that car, Dean pulled out his phone and looked at it's clock only to find that it was wayyy later than he had thought.

He rolled out from under the car using Sam’s old skateboard and used his shirt to wipe the sweat off his brow. He got up and realized something _so profound, so exquisite,_ it had him stop in his tracks; _he really needed to take a piss._

He could easily go inside and use the bathroom by the kitchen’s back door. However, he was dead tired and he wasn’t really thinking straight so instead of doing the logical thing, he went by the nearest tree in his backyard, the one right by the path that connected his neighbor's and his house, he whipped his dick out and then promptly proceeded to have one of the most satisfying outdoor peeing experiences he had ever experienced.

It was also the last time he ever peed outside.

“Hey mister, what’re you doing to that tree?” Asked an unfamiliar high pitched voice right behind Dean.

Dean screamed ~~like a man~~ because this person caught him by surprise and in the heat of the moment, he turned around, dick in hand and accidentally assaulted his intruder by peeing on him. He couldn’t help it, he couldn’t even stop his flow once he started going. Unfortunately for Dean, the person who fell victim to his urine attack was none other than his neighbor’s six year old son, Stiles Stilinski. Whose father also happened to be the Sheriff.

And just to prove just how f _ucked_ Dean was, the Sheriff himself stepped outside of his suburban house and saw him.

He saw his neighbor, _Dean Winchester, pissing on his beloved only son._

_“What the hell-“_

“Turn it off, turn it off! I’m not in my bathing suit!”

“Oh my god, no no no this isn’t what it looks like oh my god I’m trying to stop!” Dean screeched just as his penis finally fucking _stopped god damn it._

“ ** _Enough!”_** Sheriff Stilinski yelled as he glared at Dean.

 

 ~~Dean literally felt his balls shrivel up.~~ He shook his cock really quick and stuffed it down his pants as fast he could, even hurting himself in the process but he refused to wince. He’d try to run away but the situation was bad enough and the Sheriff _definitely_ knew where he lived. Dean clenched his jaw in embarrassment especially since he was sporting a furious blush and he refused to look the Sheriff in the eyes.

The Sheriff gave a weary sigh and said “Stiles, go inside and go run a bath for yourself. I’ll be there shortly to help you. Mr. Winchester and I are gonna have us a _chat.”_

Dean looked up in alarm because he was pretty sure he was about to take a trip to the precinct and he just _knew he’d never hear the end of it from Sam._


	2. Staircase Stories

 

“Explain yourself and _fast,_ ” the Sheriff demanded as he stood tall with his arms crossed over his chest and _very noticeable badge._

 

Dean started to sweat which made him worry that the Sheriff would take that as an admission of guilt and he wasn’t guilty!

 

“Look, I was just peeing on my tree when _your son showed up out of nowhere_ and scared the shi-crap out of me _and I swear I didn’t mean to pee on him, I swear!”_ Dean rambled.

 

The Sheriff narrowed his eyes at Dean. He’d seen Dean grow up and he knew he was a good student, a good brother and an all-around good person.

 

“You know I could charge you with indecent exposure?”

 

Dean gulped.

 

“However, I’m running late for a very important town meeting, I’ve got _absolutely no one_ to babysit Stiles and I believe you, so I won’t,” Sheriff Stilinski said, giving Dean a significant look.

 

It took Dean a couple but he got there.

 

“Oh uh Sir! I could babysit Stiles for you,” he said all at once.

 

“Huh, well I guess that’s okay. I’ll be getting home around ten, his bed time is at eight and there’s a list of numbers on the refrigerator in case of emergencies. We’ll talk more about this,” Sheriff Stilinski said pointing at the space where Dean had his _incident,_ “Later.”

 

He walked back into the house after that which made Dean let out a breath of relief. Moments later, the Sheriff walked back out of the house and reminded Dean he’d be back by ten. Wishing him fun, the Sheriff got into his police car and left Dean alone in the Stilinski’s empty drive way. He took a deep breath and braced himself as he walked to the Stilinski’s front door. It was unlocked, just like he had expected it would be and sitting on the staircase in freshly put on pajamas, was Stilinski’s kid.

Dean approached the staircase like one would approach a small woodland creature who was easily spooked.

 

“Heyyy, buddy,” Dean said awkwardly.

 

He cleared his throat and stuck out his hand for a hand shake.

 

“You peed on me, didn’t you?” Stiles asked with narrowed eyes.

 

_Of course he’d bring it up._

 

“Look kid, I won’t lie to you. Mistakes were made and you got peed on. But is it really my fault? I mean, you did kinda sneak up on me while I was doin my business.”

 

“I thought you were kissing the tree!” Stiles exclaimed in his high pitched little kid voice.

 

“Why would I be kissing a tree? I’m not that unattractive,” Dean said, hoping to change the subject.

 

“Why were you even peeing on that tree? Don’t you have a bathroom in your house?” Stiles asked, not cutting Dean _any_ slack.

 

Dean sighed.

 

“Look, I was feeling lazy so I just peed on the nearest thing. Trust me, I’m not exactly gonna ever do it again,” Dean said.

 

“Were you marking your territory? My teacher Ms. Summers said that’s what dogs do. Are you a dog?” Stiles asked seriously.

 

“No, I’m a Dean. I’m a one of a kind, very limited edition kind of deal,” Dean said in response.

 

“So what did my dad tell you?” Stiles asked, swinging his legs through the staircase railing.

 

Dean sat down next to him and went as far as sticking his own legs through the railing’s bars.

 

“He told me that you needed a babysitter, so I volunteered.”

 

“Like Katniss?”

 

“Exactly like Katniss.”

 

“But why would my dad let a pee monster babysit me?”

 

Dean groaned in frustration. The urge to hit his head against the railing was becoming very appealing but his image was already damaged enough. He didn’t need this kid to think he was crazy. It was by a stroke of luck that Dean remembered an old tactic he use to use on Sam when he had wanted Sam to forget about something.

 

“Wanna hear a scary story?”

 

“ _No! I mean yes”_ Stiles said a bit too fast.

 

Dean smiled because he knew he had won.

 

“You sure? Because I’d understand if you didn’t want to listen to this story. I mean, most babies are too scared to listen to this story and you look like the biggest baby I’ve ever seen.”

 

“I'm not a baby!” Stiles squawked, his lips forming an instant pout.

 

“Oh so you wanna listen to the scary story?”

 

“Ye-yeah,” Stiles said despite the tremor in his voice.

 

Dean smiled like the Cheshire cat because _he knew he got him._

 

“Ever hear about _the sponge?”_ Dean asked in a low voice.

 

“ _Th-the sponge?”_ Stiles repeated as his lips quivered in fear.

 

“The sponge,” Dean confirmed.

 

Stiles withdrew from the railing and sat on the staircase normally. He grabbed a blanket next to him that had been hidden from Dean’s line of vision. He covered himself and Dean, who had done the same as him and was now sitting in front of him. Dean waited until they were both completely settled to continue.

 

“Most people think that the scariest place in this town is the woods,” Dean said intensely.

 

“They’re not?” Stiles asked interrupting Dean.

 

“No, they’re not and don’t interrupt me that’s rude, anyways, the woods in town are by far _not_ the scariest place in this town. It’s not even your closet,” Dean said menacingly.

 

Stiles gulped as he clutched his blanket.

 

“It’s not even the space under your bed,” Dean said in a silky soft voice.

 

“What is the scariest place?” Stiles asked even though he knew the answer would terrify him.

 

Dean pretended to look around to make sure no one was listening. Stiles did the same. When he ‘deemed it safe’, Dean turned to look Stiles dead in the eyes.

 

“It’s the sink, you know, where they _drown babies_ ,” Dean said dramatically.

 

 

Dean spent twenty minutes calming down a hysterical Stiles who had made him swear to never tell him another scary story or to ever drown him. Dean swore even though he realized how ridiculous the whole situation was. He realized too late he had taken it too far with the story. Christ, Stiles was only six. Dean gripped the bridge of his nose. He had a headache and he thanked the lord that Stiles had knocked out. The only way he was able to calm Stiles down was by watching Lilo and Stitch two times in a row. It was a nightmare.

Dean had carried him up the stairs and tucked him into his bed. Sleeping with a toy fox clutched to his chest, Stiles looked adorable. Dean almost forgot _how fucking annoying Stiles was._ The image made Dean reminiscent of when Sam was younger and how Dean had taken care of him. Now Sam was twelve, already ahead of the game and preparing for the future.

More so than Dean was and Dean was the oldest.

 

The sound of a lock being turned was heard and Dean looked up from his spot on the stairs to see the Sheriff standing in the door way with a bunch of files in one hand.

 

“Rough meeting?” Dean asked.

 

The Sheriff rubbed his jaw and said “Something like that. How about you?”

 

“It was alright,” Dean said, chuckling to himself.

 

The Sheriff gave him a tired grin.

 

“He’s a handful, I know. But he’s such a good kid.”

 

Dean nodded his head in agreement.

 

“So Dean, you’re free to go,” the Sheriff said opening the door for him.

 

Dean got up from the stairs and said “Really? I mean, thank you, sir. I promise this won’t happen again.”

 

“I would hope not,” the Sheriff said amused.

 

Dean blushed as he left the house but he left feeling relieved and yet, he felt like he was missing something.

 

Later he would say what he was missing was his sanity.

**Notes for the Chapter:**

> Ah yes, comments are appreciated. I almost died writing this.


	3. Deal Or No Deal

**Notes for the Chapter:**

> I'm sorry I'm such a late hoe but like adulthood is hard, okay?

“First things first: you and I? We’re not friends. This is a business transaction. I hang out with you and then I get _money_ so I can fix my sick ass car and then get sick ass babes in that car,” Dean said crouched in front of Stiles Stilinski, the kid he was now going to be seeing till the end of time.

 

It was weird how looking into Stiles’ little tiny face nodding profusely made Dean understand why people sold their soul to the Devil.

 

“There’s going to be rules, so wipe that smile off your face, no one’s ever happy over rules,” Dean said as he narrowed his eyes at Stiles who looked like he could barely contain his excitement.

 

“No, but Dean, I like rules. Ms. Summers says rules are important and it’s why humanity is still around and Dinosaurs are dead,” Stiles answered.

 

_Jesus fucking Christ_ , this was gonna be a nightmare.

Earlier that day…

Dean walked down the  familiar creaky Singer stairs as he made his way to the kitchen to make himself breakfast. Babysitting Stiles has apparently taken a lot out of him so when he finally made it home, he ended up crashing instead of staying up all night playing Skyrim with Benny.

Dean smiled softly, scratching his stomach as he remembered how easily he was able to strip himself down to his boxers and knock out peacefully. It had been a long time since Dean had been able to sleep so soundly without being haunted by horrible nightmares.

He smiled even more at how dark the living room was. Dean thanked Mary, Joseph, Guadalupe and Jesus that his Uncle had the blinds for all the windows closed. Sunlight would’ve definitely ruined his easy going vibe he was feeling as a side effect from a good night’s sleep and while he was pretty sure the blinds were pulled down due to his Uncle’s paranoia rather than his hatred of sunlight, Dean was nevertheless happy.

He sniffed the air when the scent of bacon hit him and with the finality of smacking his lips, he finally made his way into the kitchen. With bleary eyes, Dean found the coffee pot brewing in it’s normal spot. He made a delighted noise and poured himself a cup, only pouring a generous amount of sugar before taking a sip. It was hot and it wasn’t the best coffee he’d ever had, but shit, it felt like coming home.

 

“Do you want a room for you and that coffee?” A familiar voice said, efficiently cutting off the moan Dean had made when the coffee hit his lips.

 

Dean froze and turned to the dining table to find both his Uncle Bobby and The fucking Sheriff sitting at his dining table looking at him with equal amounts of disbelief and an eyebrow raised in question.

 

Dean smiled sheepishly and said “Um, sorry, thought I was alone. Good morning, Sheriff.”

 

“Mornin’ to you too, Dean,” The Sheriff said, smirking slightly.

 

It’s then that it dawned on Dean that he was only clad in boxers and really, how many times did the Sheriff have to see him in compromising positions. Dean contemplated running to the security of his room but that idea was shot to hell when-

 

“The Sheriff here was just telling me about some of the _wildest_ things I’ve heard in awhile. Why, he was telling me that he recently had to deal with the desecration of one of the trees in his backyard,” Bobby said dryly with a knowing look.

 

Dean asked God what he ever did to him for this while the Sheriff pulled out a chair from the table and motioned for Dean to sit.

 

“So since I’m not going to formally press charges of indecent exposure despite the fact that this will somehow come back to ultimately traumatize my son, I’m willing to have you punished in some other form,” The Sheriff said when Dean took a seat.

 

Dean groaned and put his face in his hands.

 

“Stiles...Stiles has had a few, well, a couple of _difficulties_ with his other babysitters. He liked you and since I know you and you need to do time, you’re going to be babysitting my son from now on.”

 

At this, Dean looked up at the Sheriff in confusion.

 

“What? Shouldn’t I be like the last person to babysit him?” Dean blurted out.

 

Bobby rolled his eyes and said “You needed a job and the Sheriff is being nice enough to be giving you one. Actually, you don’t have a choice. So you’re either babysitting the kid or you’re getting _pee offender_ on your permanent record.”

 

“When can I start?”  

****  
  


So cue Dean, now standing in front of an overly happy snot nosed kid who looks like he’s about to puke up rainbows because Dean just told him he was going to be picking him up from school and staying with him until his dad came home from work at six.

 

“And we’re gonna make pillow forts and we can draw things together and we can cut each other’s hair and I’ll pull your teeth and you’ll pull mine and we can watch Lilo&Stitch **_forever_**!”

Cas was never going to stop laughing at him.

 

**Author's Note:**

> I'd love some feedback for this, so leave some comments


End file.
